CN102473854B - Deposition material for organic device and method for producing organic device - Google Patents
Deposition material for organic device and method for producing organic device Download PDFInfo
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- CN102473854B CN102473854B CN2010800331451A CN201080033145A CN102473854B CN 102473854 B CN102473854 B CN 102473854B CN 2010800331451 A CN2010800331451 A CN 2010800331451A CN 201080033145 A CN201080033145 A CN 201080033145A CN 102473854 B CN102473854 B CN 102473854B
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- 239000000463 material Substances 0.000 title claims abstract description 259
- 230000008021 deposition Effects 0.000 title claims abstract description 207
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- 238000002360 preparation method Methods 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 48
- 239000012044 organic layer Substances 0.000 claims description 23
- 238000000859 sublimation Methods 0.000 claims description 19
- 230000008022 sublimation Effects 0.000 claims description 19
- 238000000746 purification Methods 0.000 claims description 18
- 150000002894 organic compounds Chemical class 0.000 claims description 16
- -1 amine compound Chemical class 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 12
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 241001597008 Nomeidae Species 0.000 claims description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical class [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- 239000010406 cathode material Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
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- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
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- 239000010405 anode material Substances 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
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- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
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- JNNSNERDBYHJEO-UHFFFAOYSA-N benzene;9h-carbazole Chemical compound C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 JNNSNERDBYHJEO-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
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- 239000012159 carrier gas Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920003050 poly-cycloolefin Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical class C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
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- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
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- C23C14/24—Vacuum evaporation
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- H10K71/10—Deposition of organic active material
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- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract
A deposition material which is used for producing an organic device, wherein the deposition material has an average particle diameter of 10 [mu]m to 200 [mu]m where the average particle diameter is expressed by D50% and has a uniformity degree of 1.0 to 4.0 where the uniformity degree is expressed by D60% diameter/D10% diameter.
Description
Technical field
The present invention relates to the deposition materials as organic electroluminescent element, organic thin film solar cell, organic field effect tube for organic assembly, and for using described deposition materials to prepare the method for organic assembly.
Background technology
In order to obtain the purpose of practical application, too much plant after deliberation the organic assembly that uses organic compound, comprise organic electroluminescent device.The film that organic assembly is formed by the organic deposit material that contains organic compound by deposition usually forms, to such an extent as to the performance of resulting organic assembly can be affected by the deposition rate of used deposition materials.
Therefore, studied the deposition materials for organic assembly with some conventional arts.
For example, some have partical (pelleted) the organic deposit material of the gas content below 1 % by mole to form organic layer (referring to patent documentation 1) to propose the suggestion deposition.
Yet, have some problems for top advised partical organic deposit material: they are too large and be difficult to bear the heat treatment in deposition process dimensionally, because partical organic deposit material is by being prepared by given shape by particle organic deposit material cured.
Also advised for by powder that organic distil powder and heat conduction can not be distilled, mixing the method (referring to patent documentation 2) for preparing partical organic deposit material.
Even use the wherein partical organic deposit material of suggestion to contain can not the distil method of powder of heat conduction, in any case, can not successfully overcome above problem,, be difficult to bear the heat treatment in deposition process, thereby and, may further cause another problem: be difficult to them with stable deposition rate deposition.Variation on deposition rate can cause the variation on the organic assembly performance, causes the great changes on film thickness simultaneously when formation has the organic layer of large area, thereby and, the accessory problem that this may cause productive rate to descend.
Reference listing
Patent documentation
Patent documentation 1: Japanese Patent Application Publication (JP-A) number 11-92915
Patent documentation 2:JP-A 2003-115381
Summary of the invention
Technical problem
The object of the invention is to solve above existing issue and obtain following target.Particularly, a target of the present invention is to provide such deposition materials: the ability that has outstanding deposition rate stability and be formed uniformly the large tracts of land film that contains organic compound reduces the variation on the performance of resulting organic assembly simultaneously; And a kind of for using described deposition materials to prepare the method for organic assembly.The scheme of dealing with problems
As follows for the means that overcome the above problems.
<1 > a kind of deposition materials for the preparation of organic assembly, wherein said deposition materials has the average grain diameter of 10 μ m to 200 μ m, wherein said average grain diameter means by D50%, and described deposition materials has 1.0 to 4.0 the uniformity, the wherein said uniformity means by D60% diameter/D10% diameter.
<2 > according to<1 > described deposition materials, wherein said deposition materials contains organic compound or inorganic oxide.
<3 > according to<1 > or<2 > described deposition materials, wherein said deposition materials is used to form at least one organic layer between the pair of electrodes that is arranged on organic electroluminescent device.
<4 > according to<3 > described deposition materials, wherein said organic layer is luminescent layer.
<5 > according to<4 > described deposition materials, described deposition materials also comprises Ir complex or Pt complex.
<6 > a kind of method for the preparation of organic assembly, described method comprises:
By the flash deposition according to<1 to<5 in the described deposition materials of any one to form organic layer.
<7 > a kind of organic assembly, described organic assembly is by basis<6 > the described acquisition of the method for the preparation of organic assembly.
The beneficial effect of the invention
The present invention can provide: a kind of deposition materials, and described deposition materials shows outstanding deposition rate stability and the ability that is formed uniformly the deposited of large area that contains organic compound, and reduces the variation on resulting organic assembly performance; And a kind of for using described deposition materials to prepare the method for organic assembly.These can solve above Problems Existing and obtain above target.
The accompanying drawing summary
Fig. 1 is the viewgraph of cross-section of the representative configuration of organic electroluminescent device.
Fig. 2 is the luminous figure over time that has shown organic electroluminescent device.
Embodiment describes in detail
(for the deposition materials of organic assembly)
According to the deposition materials for organic assembly of the present invention (organic assembly deposition materials or deposition materials) simply, it is the deposition materials for the preparation of organic assembly, described deposition materials has the average grain diameter of 10 μ m to 200 μ m, wherein said average grain diameter means by D50%, and described deposition materials has 1.0 to 4.0 the uniformity, the wherein said uniformity means by D60% diameter/D10% diameter.This deposition materials preferably passes through sublimation purification.
The average grain diameter meaned by D50% is 10 μ m to 200 μ m, preferably 20 μ m to 180 μ m, more preferably 40 μ m to 150 μ m, particularly preferably 50 μ m to 120 μ m.
When the average grain diameter meaned by D50% is less than 10 μ m, may cause static and increase the contact between particle by the gathering of particle, be difficult to so become the deposition rate that keeps stable.On the contrary, when average grain diameter is greater than 200 μ m, the variation on the unit interval deposition can increase, and becomes and be difficult to the deposition rate that keeps stable.
As used herein, D50% refers to average grain diameter, and the amount that wherein particle diameter is greater than the powder of average grain diameter D50% equals the amount that particle diameter is less than the powder of average grain diameter D50%.
The average grain diameter meaned by D50% (hereinafter also referred to as " average grain diameter ") can be determined by read in 50% the data point of passing through percentage or accumulative perception from grading curve.Can pass through any means curve of grain size curve chart, described method comprises, but specifically be not defined in: screening sample, the percentage % of the sieve aperture μ m passed with study sample and the sample passed, in order to using sieve aperture as trunnion axis and the method as the vertical axis mapping by percentage of usining; And the method for measuring cumulative distribution by the laser diffraction granularity distribution instrument.
By the uniformity (hereinafter also referred to as " uniformity ") that the D60% diameter/the D10% diameter means, be 1.0 to 4.0, preferably 1.0 to 3.5, more preferably 1.0 to 3.2, particularly preferably 1.0 to 3.0.
Can not realize being less than 1.0 the uniformity in theory.On the contrary, when the uniformity is greater than 4.0, the variation on the unit interval deposition may increase and become and is difficult to the deposition rate that keeps stable.
As used herein, the D60% diameter refers to such particle diameter: under this particle diameter on grading curve pass through percentage or accumulative perception is 60%, and the D10% diameter refers to such particle diameter: under this particle diameter on grading curve pass through percentage or accumulative perception is 10%.
Can carry out by any method the measurement by D60% diameter/uniformity that the D10% diameter means, described method comprises, but specifically be not defined in, use triage techniques or laser diffraction granularity distribution instrument take to obtain grading curve and read afterwards by percentage or accumulative perception the particle diameter that is 60% and 10% place in resulting grading curve, with the uniformity that is compared to of the particle diameter at the particle diameter that calculates 60% place and 10% place.
Can depend on the expection purpose suitably select for the preparation of the method had as the deposition materials of top defined average grain diameter and the uniformity.The example comprises, but specifically is not defined in, and wherein material ground in mill, via the sieve with obtaining the hole required with the deposition materials of controlled average grain diameter as above and the uniformity, it sieved to obtain the method for deposition materials afterwards.
Comprise for the method that deposits this deposition materials, but specifically be not defined in, resistance heating method and flash deposition process, and the flash deposition process is preferred.Even while depositing under the deposition rate increased, should also can provide reliable deposited film for the deposition materials of organic assembly, and because its stability outstanding on deposition rate can deposit long-term and stably.
About the flash deposition process, even by the deposition materials that tends to due to long-time heating decompose, can not decomposed by stably depositing continuously yet.In addition, the deposition materials that contains inorganic oxide can form the film with the composition that is similar to deposition materials.Any material that to describe in the part of " for the preparation of the method for organic assembly " can be for the flash deposition technique.
Can depend on the expection purpose and suitably select for the deposition materials of organic assembly without any restriction especially, as long as it meets as the top defined needs for average grain diameter and the uniformity, and described deposition materials includes organic compounds and inorganic oxide, as luminescent material, material of main part, dopant material.Suitable is the material through sublimation purification.
Here, phrase " sublimation purification " refers to the difference on sublimation temperature between a kind of based target compound and impurity and purifying process that they are separated.Mode for sublimation purification is not particularly limited.Can depend on production scale and working condition and suitably select any sublimation purification equipment.Can be by making gas flow and strictly controlling the purity increase that temperature completes resulting target compound.
Can depend on that the expection purpose suitably selects organic compound and without any special restriction, and the mixture of organic compound preferably.
-luminescent material-
Luminescent material can be fluorescent material and phosphor material, and their two or more mixture.
Aspect the driving durability, light-emitting dopant is preferably the dopant that meets following relation with respect to host compound: the difference Δ Ip:1.2eV of ionization potential>Δ Ip>0.2eV, and/or the difference Δ Ea:1.2eV of electron affinity>Δ Ea>0.2eV.
The gross mass of the compound based on forming luminescent layer, in luminescent layer the content of light-emitting dopant preferably in the scope of 0.1 quality % to 50 quality %, more preferably 1 quality % to 50 quality %, particularly preferably 2 quality % to 40 quality % aspect external quantum efficiency.
-phosphor material-
Can depend on that the expection purpose suitably selects phosphor material, described phosphor material comprises, but specifically is not defined in, the complex that contains transition metal atoms or lanthanide series atom.
Can depend on that the expection purpose suitably selects transition metal atoms, described transition metal atoms comprises, but specifically is not defined in, ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, gold, silver, copper and platinum.In them, more preferably rhenium, iridium and platinum, and particularly preferably be iridium and platinum.
The part of complex can comprise with the part described in Publication about Document: such as G.Wilkinson etc., and comprehensive Coordinative Chemistry (Comprehensive Coordination Chemistry), Pergamon Press (1987); H.Yersin, " photochemistry of complex and photophysics (Photochemistry and Photophysics of Coordination Compounds) ", Springer-Verlag (1987); And Akio Yamamoto, " organometallic chemistry basis and application (Organometallic Chemistry-Basis and Application-) ", SHOKABO PUBLISHING Co., Ltd. (1982).
Complex can contain a transition metal atoms, or can contain two above transition metal atoms; That is, can be usually said polynuclear complex.Complex can also contain different metals simultaneously.
Phosphor material can be, for example U.S. Patent number 6303238 and 6097147; International application no WO00/57676, WO00/70655, WO01/08230, WO01/39234, WO01/41512, WO02/02714, WO02/15645, WO02/44189, WO05/19373, WO2004/108857, WO2005/042444 and WO2005/042550; JP-A 2001-247859,2002-302671,2002-117978,2003-133074,2002-235076,2003-123982 and 2002-170684; European patent number 1211257; And the phosphor material described in JP-A 2002-226495,2002-234894,2001-247859,2001-298470,2002-173674,2002-203678,2002-203679,2004-357791,2006-93542,2006-261623,2006-256999,2007-19462,2007-84635 and 2007-96259.
In them, following complex preferably: as Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex and Ce complex, and particularly preferably be Ir complex and Pt complex.
Each complex preferably contains at least one coordination mode that is selected from the following: metal-carbon key, metal-nitrogen key, metal-oxygen key and metal-sulfur key, and aspect luminous efficiency, organic assembly driving durability and colourity, more preferably contain multidentate ligand, as the complex of the above part of three teeth.
The preferred embodiment example of Ir complex and Pt complex is as follows.
-fluorescent material-
Can depend on that the expection purpose suitably selects fluorescent material, and the example comprises, but specifically be not defined in benzo
azoles, benzimidazole, benzothiazole, styryl benzene, polyphenyl, diphenyl diethylene, tetraphenylbutadiene, naphthalimide, coumalin, pyrans, pyrene ketone (perinone),
diazole, aldazine, pyrrolidines, cyclopentadiene, two-styryl anthracene, quinacridone, pyrrolopyridine, thiadiazoles pyridine, cyclopentadiene, styrylamine, aromatics two methylidyne compounds; The fused polycycle aromatic compounds is as anthracene, phenanthroline, Bi, perylene, rubrene or pentacene; Metal complex containing oxine; Take the various metals complex that pyrroles's methine complex (pyrromethene complexes) and rare earth metal complex be representative; Polymerizable compound is as polythiophene, polyhenylene and polyphenylene vinylene; Organosilan, or derivatives thereof.Can be used alone or in combination these fluorescent materials.
-material of main part-
Material of main part is preferably charge transport material.Can be used alone or in combination material of main part.
As material of main part, can use the cavity conveying material of main part with outstanding cavity conveying ability and the electron transport material of main part with outstanding electron transport ability.
--cavity conveying material of main part--
Can depend on that the expection purpose suitably selects the cavity conveying material of main part, described cavity conveying material of main part comprises, but specifically be not defined in pyrroles, indoles, carbazole, azaindole, azepine carbazole, triazole,
azoles,
diazole, pyrazoles, imidazoles, thiophene, poly-aromatic yl paraffin, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino chalcone, styryl anthracene, Fluorenone, hydrazone, Stilbene, the silazane replaced; The aromatic uncle amine compound; Styrylamine compound, aromatics two methylidyne compounds; Porphyrin compound; Polysilane compound; Poly-(N-vinylcarbazole); Aniline; Conducting polymer is as thiophene oligomers and polythiophene; Organosilan; Carbon film; And their derivative.Can be used alone or in combination the cavity conveying material of main part.
In them, indole derivatives preferably, carbazole derivates, aromatic uncle amine compound and thiophene derivant, more preferably in molecule, there is the compound of carbazole group, and particularly preferably be the compound of the carbazole group that there is tert-butyl group replacement in molecule.
--electron transport material of main part--
Can depend on that the expection purpose suitably selects the electron transport material of main part, described electron transport material of main part comprises, but specifically is not defined in, pyridine, pyrimidine, triazine, imidazoles, pyrazoles, triazole,
azoles,
the compound that diazole, Fluorenone, anthraquinone bismethane, anthrone, diphenyl quinone, thiapyran dioxide, carbodiimide, fluorenylidene methane, diphenylethyllene pyrazine, aromatics fluorine replace; The heterocycle tetracarboxylic anhydride is as the Nai perylene; Phthalocyanine or derivatives thereof (it can form fused rings with another ring); And with the metal complex of oxine derivative with contain metal-phthalocyanine, benzo
the various metals complex that azoles and benzothiazole are representative as the metal complex of part.Can be used alone or in combination this electron transport material of main part.
Among them, metal complex preferably aspect durability, and more preferably contain at least one metal complex as the part with metal-complexing in nitrogen-atoms, oxygen atom and sulphur atom.
The representative instance of metal complex for example comprises, the compound of describing in JP-A 2002-235076,2004-214179,2004-221062,2004-221065,2004-221068 and 2004-327313.
The example that can be used for cavity conveying material of main part of the present invention and electron transport material of main part can include, but are not limited to following compound and their deuterated material.
-dopant material-
Can depend on suitably chosen dopant material and without any special restriction of expection purpose, and can be to be subject to electron adulterated dose and to any one in electron adulterated dose.
Arbitrarily inorganic compound and arbitrarily organic compound can be used for being subject to electron adulterated dose and without any special restriction, as long as it has the function that is subject to electronic property and oxidation of organic compounds.
This inorganic compound can comprise metal halide, and metal oxide.
Metal halide comprises iron chloride, aluminium chloride, gallium chloride, inidum chloride and Antimony pentachloride.
Metal oxide comprises vanadium pentoxide and molybdenum trioxide (MoO
3).
The example of above organic compound comprises having separately nitro, halogen atom, cyano group and trifluoromethyl as substituent compound; Naphtoquinone compounds; Acid anhydrides; And fullerene.
Give electron adulterated dose and preferably include, but be not limited to, alkali metal as Mg, the transition metal that comprises rare earth and organic reducing compound, needs only the ability that it has electron donation and reduction organic compound as Li, alkaline-earth metal.Be preferred for metal of the present invention and comprise the metal that especially there is the following work content of 4.2eV, for example Li, Na, K, Be, Mg, Ca, Sr, Ba, Y, Cs, La, Sm, Gd and Yb.The organic reducing compound comprises nitrogen-containing compound, sulfur-containing compound and phosphorus-containing compound.
Alternatively, as the example of hole barrier materials, can comprise that aluminum complex is as BAlq; Triazole derivative; Phenanthroline derivative is as BCP.
(for the preparation of the method for organic assembly)
For the preparation of the method according to organic assembly of the present invention, comprise by using the flash deposition technique, and if the step deposition deposition materials for organic assembly according to the present invention as above that needs other to form organic layer.
Form the deposition technique of film when the flash deposition technique refers to and provide deposition materials continuously with powder type on the heating part of sources of deposition, it has and makes it possible to prevent the benefit of deposition materials owing to the decomposition of the composition mismatch of deposition materials and long-term heating.
Can depend on the expection purpose suitably to select pressure in the flash deposition process and without any special restriction, and preferably 10
-1pa to 10
-8pa, more preferably 10
-3pa to 10
-7pa, particularly preferably 10
-4pa to 10
-6in the scope of Pa.
When pressure lower than 10
-8during Pa, although can prevent carrying under one's arms of impurity and undesired gas, may need many days to reduce the pressure under vacuum, so cause productivity ratio to descend.When pressure is greater than 10-1Pa, may be difficult to make vaporized deposition materials to be deposited on substrate, so bring the very big decline of deposition materials utilization ratio.Alternatively, can introduce inert carrier gas as nitrogen and argon in order to control vaporized deposition materials the flowing to substrate from sources of deposition.
Can depend on that deposition materials is suitably selected heating-up temperature in the flash deposition process and without any special restriction.
Can depend on the expection purpose suitably to select deposition rate in the flash deposition process and without any special restriction and preferably at 0.01nm/s to 10nm/s, more preferably 0.1nm/s to 5nm/s, particularly preferably in the scope of 0.5nm/s to 2nm/s.
When deposition rate can be when being less than 0.01nm/s, thereby may need the time to form film and cause productivity ratio to descend.When deposition rate can when be greater than 10nm/s, may be difficult to keep the stability of deposition rate and be difficult to controlling diaphragm thickness.
As used herein, unit " nm/s " can use " dust/s " to mean, i.e. 0.1nm/s.
About the deposition rate in the flash deposition process, when deposition rate be take nm/s during as unit representation as v, if by minimum record deposition rate take nm/s as unit definition be v
minimumand will be the highest record deposition rate take nm/s as unit definition be v
maximum, take so nm/s as unit definition be v
minimum-v
? greatlythe stability boundary of deposition rate can change and without any special restriction, for example, preferably 0nm/s to 0.3nm/s, more preferably 0nm/s to 0.2nm/s, particularly preferably 0nm/s to 0.1nm/s.
When the stability boundary of deposition rate can be when being greater than 0.3nm/s, preparation stability, productive rate and device performance may descend.
Can depend on that the expection purpose suitably selects other steps and, without any special restriction, described other steps are included in any step of the preparation method for organic assembly known in the art.
This use for the deposition materials of organic assembly can be in the situation that the color stability that goes out of deposition rate be formed uniformly the large tracts of land film that contains organic compound, reduce the variation on the performance of organic assembly simultaneously, and therefore be suitable for the preparation of organic electroluminescence device, organic thin film solar cell and organic field effect tube.
Among organic assembly, particularly preferably be and be applied to organic electroluminescence device.
Typically, organic electroluminescence device needs high brightness, because can find that its brightness in time descends.Especially, have been found that in traditional electroluminescent device brightness logarithm in time descends, the initial stage is reduced (initial decrease), so produce very early significantly reduced brightness (referring to Fig. 2).It becomes the subject matter about the quality of organic assembly.
Yet, wherein by using according to the electroluminescent device of the formation of the deposition materials for organic assembly organic layer of the present invention, can the inhibition initial stage reduce (referring to Fig. 2).
Reason is because when increase during the variation on deposition rate, the mixing ratio of the concentration of guest materials and the concentration of material of main part may depart from special set point in luminescent layer, so that can not reach expected durability, by using the method according to this invention, control exactly that deposition rate is stable can provide with higher productive rate the high-performance organic assembly.
Using according to aspect the organic assembly prepared for the deposition materials of organic assembly of the present invention preferred, will be described hereinafter organic electroluminescence device.
(electroluminescent organic material)
Organic electroluminescence device can be between a pair of electricity contain at least one organic layer, and described organic layer can be made by the deposition materials for organic assembly according to the present invention.
Can depend on the expection purpose suitably select organic layer structure and without any special restriction, and comprise luminescent layer, hole injection layer, hole transporting layer, electron injecting layer, electron supplying layer, hole blocking layer, electronic barrier layer and further contain on demand other the layer.
<luminescent layer >
Luminescent layer is to have the layer of accepting from the function in the hole of anode, hole injection layer and hole transporting layer, accepts the electronics from negative electrode, electron injecting layer and electron supplying layer simultaneously, serves as again place in conjunction with hole and electronics so that luminous.
Luminescent layer can be comprised of above-mentioned luminescent material and other material of main part.In other words, luminescent layer can be formed or is combined and form to form mixed layer with material of main part by luminescent material by luminescent material itself.
In addition, luminescent layer itself can not have charge-transporting or can contain therein not luminescent material.
Can depend on the expection purpose suitably select luminescent layer thickness and without any special restriction, and preferably in the scope of 2nm to 500nm, more preferably 3nm to 200nm, particularly preferably 5nm to 100nm aspect external quantum efficiency.In addition, may have one or more luminescent layer, and luminescent layer can be luminous with different glow colors respectively in addition.
<hole injection layer and hole transporting layer >
Each of hole injection layer and hole transporting layer is to have any from anode and anode-side to accept hole and carry afterwards the layer of hole to the function of cathode side.
Each of hole injection layer and hole transporting layer can and be subject to electron adulterated dose to form by above-mentioned cavity conveying material of main part.
Can depend on the expection purpose suitably select hole injection layer and hole transporting layer each thickness and without any special restriction, and preferably at 1nm to 500nm, more preferably 5nm to 200nm, particularly preferably in the scope of 10nm to 100nm.
The single layer structure that each thickness of hole injection layer and hole transporting layer can be comprised of one or more materials, or by thering are same composition and a plurality of layers of a kind of sandwich construction formed in different the composition.
<electron injecting layer and electron supplying layer >
Each of electron injecting layer and electron supplying layer is to have from any of negative electrode and cathode side to accept hole and carry afterwards the layer of hole to the function of anode-side.
Electron supplying layer can and be given electron adulterated dose by above-mentioned electron transport material of main part and form.
Can depend on the expection purpose suitably to select thickness separately of electron injecting layer and electron supplying layer and without any special restriction, and be below preferred 500nm reducing aspect driving voltage.
The thickness of electron supplying layer can be preferably at 1nm to 500nm, and more preferably 5nm to 200nm, particularly preferably in the scope of 10nm to 100nm.
The thickness of electron injecting layer can be preferably at 0.1nm to 200nm, and more preferably 0.2nm to 100nm, particularly preferably in the scope of 0.5nm to 50nm.
The single layer structure that each of electron injecting layer and electron supplying layer can be comprised of one or more materials, or by thering are same composition and a plurality of layers of a kind of sandwich construction formed in different the composition.
<hole blocking layer >
Hole blocking layer is to have the layer that stops the hole that is delivered to luminescent layer from the anode-side function by entering cathode side.The organic layer can be used as in cathode side and luminescent layer adjacency arranges hole blocking layer.
Hole blocking layer can be comprised of above-mentioned hole barrier materials.
Can depend on the expection purpose suitably to select the thickness of hole blocking layer and, without any special restriction, and preferably at 1nm to 500nm, more preferably 5nm to 200nm, particularly preferably in the scope of 10nm to 100nm.
The single layer structure that hole blocking layer can be comprised of one or more materials, or by thering are same composition and a plurality of layers of a kind of sandwich construction formed in different the composition.
<electronic barrier layer >
Electronic barrier layer is to have the layer that stops the electronics that is delivered to luminescent layer from the cathode side function by entering anode-side, and the organic layer usually can be used as in anode-side and luminescent layer adjacency arranges electronic barrier layer.
Electronic barrier layer can be comprised of above-mentioned cavity conveying dopant.
Can depend on the expection purpose suitably to select the thickness of electronic barrier layer and, without any special restriction, and preferably at 1nm to 500nm, more preferably 5nm to 200nm, particularly preferably in the scope of 10nm to 100nm.In addition, the single layer structure that electronic barrier layer can be comprised of one or more materials, or by thering are same composition and a plurality of layers of a kind of sandwich construction formed in different the composition.
<electrode >
Organic electroluminescence device comprises that negative electrode and anode are as pair of electrodes.Consider the feature of organic electroluminescence device, at least one of negative electrode and anode is preferably transparent.Usually, when anode can only serve as while to organic layer, providing the electrode in hole, negative electrode can only serve as the electrode that injects electronics to organic layer.
For electrode, to its structure, structure and size, there is no particular limitation and depend on that the purposes of organic electroluminescence device and purpose suitably are selected from electrode material as known in the art.
Preferably include metal, alloy, metal oxide, conductive compound for the example of material that forms electrode, or their mixture.
-anode-
Comprise that conducting metal oxide is as the tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, tin indium oxide (ITO) and indium zinc oxide (IZO) for the example of material that forms anode; Metals like gold, silver, chromium and nickel; The mixture of metal and conducting metal oxide or layered product; Inorganic conductive material is as cupric iodide and copper sulfide; Organic conductive material is as polyaniline, polythiophene and polypyrrole; The perhaps layered product of they and ITO.Wherein, productivity ratio, high electrical conductivity and transparent aspect, conducting metal oxide preferably, and ITO most preferably.
-negative electrode-
Comprise that for the example of material that forms negative electrode alkali metal is as Li, Na, K, Cs etc.; Alkaline-earth metal is as Mg, Ca etc.; Rare earth metal is as gold, silver, zinc, aluminium, sodium-potassium-sodium alloy, lithium-aluminium alloy, magnesium-silver alloy, indium and ytterbium.These materials can be used separately, but, aspect the balance of stability and electronic injection performance, two or more materials can be used in combination aptly.
Among them, be preferred at electronic injection aspect of performance alkali and alkaline earth metal ions, and consider the material that outstanding storage stability most preferably mainly is comprised of aluminium.
The main material be comprised of aluminium refers to independent aluminium, and aluminium and the alkali metal of 0.01 quality % to 10 quality % or alloy or the mixture of alkaline-earth metal, as lithium-aluminium alloy and magnesium-aluminum alloy.
Can restrictedly by technology as known in the art, carry out the preparation of electrode especially without any, comprise that wet method is as print process and rubbing method etc.; The physics system is as vacuum deposition method, sputtering technology, ion plating etc.; Chemical method is as CDV, plasma CVD etc.Can form electrode at substrate according to the technology of suitably selecting the technology of the appropriate balance from considering the material that forms electrode.For example, when selecting ITO as anode material, can form electrode by DC sputtering technology or high-frequency sputtering technology, vacuum deposition method or ion plating.Alternatively, when selecting metal as cathode material, can or in succession use one or more cathode material to form electrode according to the sputtering technology while.
In addition, when figuratum electrode is with in formation, can be undertaken by any chemical etching technology, as photoetching, perhaps use any physical lithographic technique of laser, perhaps alternatively, also can according to vacuum deposition method or sputtering technology, carry out by applying mask thereon, or lift-off technology or print process.
<substrate >
Preferably, organic electroluminescence device is arranged on substrate, electrode and substrate directly can be connected to each other or arranges via intermediate layer simultaneously.
Can depend on the expection purpose suitably to select to be applicable to the material of substrate and, without any special restriction, and the example comprises inorganic material, mylar and organic material.
The example of inorganic material comprises the zirconia (YSZ) of stabilized with yttrium oxide; And glass is as alkali-free glass and soda-lime glass.
The example of mylar comprises PETG, poly-dibutyl phthalate and PEN.
The example of organic material comprises polystyrene, Merlon, polyether sulfone, polyarylate, polyimides, poly-cycloolefin, norbornene resin and gathers (chlorotrifluoroethylene).
For substrate, its shape, structure and size are not particularly limited and can depend on that the purposes of luminescent device and purpose suitably select.Substrate is preferably the form of plate.Substrate can be single layer structure or sandwich construction, and also can be comprised of one-component or two or more component.In addition, substrate can be transparent or opaque, and, for transparency carrier, it can be dark, water white or transparent with color.
Can the surface of substrate with and any of opposition side on the layer of anti-the steam is set, i.e. barrier layer for gases.
Be suitable for the layer of anti-the steam, the material of barrier layer for gases comprises, for example, inorganic material is as silicon nitride and silica.
Can be barrier layer for gases by using the high-frequency sputtering technology to form the layer of anti-the steam.
-other components-
Can depend on the expection purpose suitably to select to form according to other components of organic electroluminescence device of the present invention and, without any special restriction, described other components comprise passivation layer, can, resin-sealed layer and sealant.
Can depend on the expection purpose suitably to select passivation layer, can, resin-sealed layer and sealant and without any special restriction, and for example can press and arrange described in JP-A 2009-152572.
Fig. 1 is the schematic diagram according to an exemplary stratiform structure in organic electroluminescence device of the present invention.Organic electroluminescent device 10 has layer structure, its Anodic 2 (for example, the ITO electrode) be formed on glass substrate 1, and for example, by hole injection layer 3, hole transporting layer 4, luminescent layer 5, electron supplying layer 6, electron injecting layer 7 and negative electrode 8 (Al-Li electrode) according to above order lamination.Notably, anode 2 (for example, ITO electrode) and negative electrode 8 (for example, Al-Li electrode) link together via power supply.
-drive-
Organic electroluminescence device can be by applying DC (if need it, can contain the AC composition) voltage between anode and negative electrode, typically 2 volts to 15 volts or DC electric current and realize luminous.
Can use thin-film transistor (TFT) that organic electroluminescence device is applied to the active matrix scheme.As the active layer in thin-film transistor, can use amorphous silicon, high temperature polysilicon, low temperature polycrystalline silicon, crystallitic polysilicon, oxide semiconductor, organic semiconductor or carbon nano-tube.
Can by, for example, the thin-film transistor described in international publication number WO2005/088726, JP-A 2006-165529 and Application No. 2008/0237598A1 is applied to organic electroluminescence device of the present invention.
Can obtain the raising on the light extraction efficiency of organic electroluminescence device without any special restrictedly mode by multiple skill as known in the art.For example, the surface topography of substrate processing (for example, forming the microgroove pattern); Control substrate, ITO layer and the organic layer refractive index as luminescent layer; And control substrate, ITO layer and organic layer and can bring the light extraction efficiency of raising and the external quantum efficiency of increase as luminescent layer thickness separately.
Can obtain via top emission design or bottom emission mode the light extraction efficiency of organic electroluminescence device of the present invention.
Organic electroluminescence device can comprise resonator structure.For example, on transparency carrier, lamination is comprised of a plurality of laminated films with different refractivity in order many layer mirror, transparent or opaque electrode, luminescent layer and metal electrode.Each of many layer mirror and metal electrode can be served as speculum repeatedly to reflect the light from luminescent layer, thereby induces the optical resonance (first aspect) between them.
In second aspect, on transparency carrier, each of transparent or opaque electrode and metal electrode can be served as speculum repeatedly to reflect light from luminescent layer to induce the optical resonance between them.
For forming the optical resonance structure, each refractive index of the layer between the effective refractive index by two speculums and speculum and each definite optical path length of each thickness should be controlled to for obtaining the optimum value of required resonant wavelength.
In first aspect, an example of the formula for estimating optimum value has been described in JP-A 09-180883.
In second aspect, an example of the formula for estimating optimum value has been described in JP-A 2004-127795.
-application-
Can depend on the expection purpose suitably select organic electroluminescence device of the present invention, and be suitable for, for example, display element, display, backlight, electrofax, lighting source, recording light source, exposure light source, read light source, label, advertisement display, interior decoration and optical communication.Known for the certain methods of constructing full-color organic electroluminescent (EL) display, as " display monthly magazine (Monthly Display) " in September, 2000, the 33rd to 37 pages described, comprise: the three look shooting methods of launching respectively corresponding to the organic electroluminescence device of the light of three primary colors (that is, blue (B), green (G) and red (R)) are set on substrate; The white light that to launch from the organic electroluminescence device of transmitting white by colour filter is separated into trichromatic white light emission method; The blue-light-emitting that will send from the organic electroluminescence device of emission blue light is converted to the color conversion method of red (R) and green (G) via the fluorochrome layer.Can launch different some luminous organic electroluminescence devices combinations to prepare as required planar light source by what use above method to obtain, comprise the white light source that the element of element by the combined transmit blue light and emission gold-tinted is made; By the element of combined transmit blue light, the element of transmitting green light and the another kind of white light source that red-emitting moral grace element is made.
Embodiment
Next will describe the present invention in detail by the mode of embodiment, described embodiment should not be interpreted as limiting the present invention to wherein.
[preparation example 1: embodiment 1 to 6 and comparative example 1 to 7]
Use sublimation purification equipment (trade name P-100, ALS Technology Co., Ltd.) to carry out sublimation purification to the compound with following structural formula (A) as material of main part.Collect resulting product and melt in broken machine (Super mass colloider (MKCA6-2)) at ultrafine dust the space changed between grinding stone and grind to prepare and there is approximately 1,500 μ m to the about powder of the average grain diameter of 20 μ m.
For preparation has the more powder of small particle diameter, use dry-type jetting mill (NJ-50) further to grind with preparation in powder and there are approximately 20 μ m to the about powder of the average grain diameter of 1 μ m.
Have approximately 1 by resulting, the 500 μ m extremely approximately powder of the average grain diameter of 1 μ m have 1 via as described below, the sieve of the sieve aperture between 520 μ m to 1 μ m little by little sieves, to obtain the deposition materials for organic assembly of embodiment 1 to 6 and comparative example 1 to 7, described deposition materials has the average grain diameter shown in table 1 (D50%) and the uniformity (D60% diameter/D10% diameter).
Sieve aperture: between 1,520 μ m to 20 μ m
Stainless steel sift (product of Semitec Corporation)
Sieve aperture: between 15 μ m to 1 μ m
Nylon mesh (NYTAL, the product of Semitec Corporation)
Compound (A)
(measurement of particle diameter and the uniformity)
Use laser diffraction/scattering particle size analyzer (Microtrac MT3000II, the product of day machine dress society (Nikkiso Co., Ltd.)) measure average grain diameter (D50%) and the uniformity (D60% diameter/D10% diameter) according to the deposition materials for organic assembly of embodiment 1 to 6 and comparative example 1 to 7.Result provides in table 1.
(for the method for measuring deposition rate and the evaluation of deposition rate stability)
By following method, use vacuum deposition apparatus (product of Tokki Corporation) with impeller to carry out the measurement according to the deposition rate of the deposition materials for organic assembly of embodiment 1 to 6 and comparative example 1 to 7: will drop on the flash depositing member in vacuum chamber with constant rate of speed for the deposition materials of organic assembly, to be deposited into substrate from the flash depositing member for the deposition materials of organic assembly, and when the deposition rate with 12.0 dusts/s (=1.2nm/s) deposits, use film thickness monitor (CRTM-9000, Ulvac, Inc. product) measure the deposition rate that the deposition materials for organic assembly deposits on crystal oscillator, to record minimum under stable state and maximum deposition rate, described crystal oscillator is positioned at and the identical distance of leaving the flash depositing member of distance from the flash depositing member to substrate.
In addition, carry out the evaluation of deposition rate stability by following method: measure the minimum value of deposition rate and the difference between maximum, with according to following standard evaluation difference.Result provides in table 1.
The evaluation criterion of<deposition rate stability >
Below A:2 dust/s
B:2 dust/s to 3 dust/s
C: be greater than 3 dusts/s
(preparation of the organic electroluminescent device of preparation example 1)
Glass substrate 0.5mm is thick and 2.5cm * 2.5cm is placed in washing container, here by its supersound washing in the 2-propyl alcohol.Washed glass substrate like this is carried out to the UV-ozone treatment 30 minutes.On resulting glass substrate, form each layer the following describes by vacuum deposition method.Unless otherwise mentioned, by flash deposition process vapour deposition organic material.Equally, unless otherwise mentioned, the deposition rate in embodiment and comparative example is 1.2nm/s.Use crystal oscillator to carry out the measurement of deposition rate.
<anode >
Deposit ITO (tin indium oxide) to the thickness with 100nm by sputtering on glass substrate.
<hole injection layer >
On anode (ITO), by 2-TNATA (4,4 '; 4 "-tri-(N-(2-naphthyl)-N-phenyl-amino)-triphenylamines) and serve as the F4-TCNQ (2,3,5 of 1 quality % of dopant, 6-tetrafluoro-7,7,8,8-four cyano quino bismethane) codeposition has the hole injection layer of 120nm thickness with formation.
The<the first hole transporting layer >
On hole injection layer, deposition α-NPD (two [N-(1-naphthyl)-N-phenyl] benzidine) has the first hole transporting layer of 7nm thickness with formation.
The<the second hole transporting layer >
On the first hole transporting layer, the hole transporting material 1 that deposition has following structural formula has the second hole transporting layer of 3nm thickness with formation.
-hole transporting material 1-
<luminescent layer >
On the second hole transporting layer, the compound (A) that contains preparation in embodiment 1 by deposition serves as guest materials as material of main part and with the amount of the amount 10 quality % with respect to material of main part doped with phosphor material Ir (ppy) (three (2-phenylpyridine)-iridium), forms the thick luminescent layer of 30nm.
<electron supplying layer >
On luminescent layer, deposition BAlq (two-(2-methyl-oxine (quinolinolato))-4-(phenyl-phenol)-aluminium (III)) has the electron supplying layer of 30nm thickness with formation.
<electron injecting layer >
On electron supplying layer, LiF is to have the thickness of 1nm for deposition.
<negative electrode >
On electron injecting layer, place the mask pattern (this mask provides the luminous zone of 2mm * 2mm) be applicable to negative electrode, afterwards plated metal aluminium with the thickness that obtains 100nm to form negative electrode.
Thereby the layered product of preparation is placed on in the glove box of argon purge, and uses afterwards ultra-violet curing sealant (XNR5516HV, Nagase-Ciba Ltd.) sealing for stainless steel.By above step, prepared the organic electroluminescent device of embodiment 1.
The deposition materials for organic assembly that contains the compound (A) changed except use on average grain diameter and the uniformity is as the material of main part for luminescent layer, with the organic electroluminescent device of mode Preparation Example 2 to 6 in the same manner as in Example 1 and comparative example 1 to 7.
The measurement that<the initial stage reduces >
Use source measuring unit 2400 (product of Toyo Corporation), by applying DC voltage so that obtaining 2,000cd/m
2brightness, thereby according to each organic electroluminescent device of following standard evaluation:
A:10% brightness reduces the required time and is equal to or greater than 1/10 of the luminous half-life; And
B:10% brightness reduces the required time and is less than 1/10 of the luminous half-life.Result provides in table 1.
The evaluation of<film uniformity >
On 20cm * 20cm glass substrate, use different compound (A) conduct on average grain diameter and the uniformity is used for the deposition materials of embodiment 2 to 6 and comparative example 1 to 7, form film to deposit by flash, and afterwards in the upper central area at substrate of Stylus surface profiler (DEKTAK6M) and the thickness of all measuring compound on resulting glass substrate (A) film on the neighboring area of substrate to calculate the difference between them, and afterwards according to following standard evaluation:
A: difference is below 5%; And
B: difference is greater than 5%.Result provides in table 1.
Table 1
In table 1, dust/s means 0.1nm/s.
[preparation example 2: embodiment 7 to 9 and comparative example 8 to 11]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (B) with following structural formula, with preparation example 1 in the organic assembly deposition materials for embodiment 7 to 9 and comparative example 8 to 11 (preparation example 2) shown in same way as preparation table 2.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 2.
Compound (B)
(preparation of the organic electroluminescent device of preparation example 2)
Except using mCP (two-carbazole benzene (bis-carbazole benzene)) as material of main part, and the organic assembly deposition materials that contains the compound that serves as luminescent material (B) changed for embodiment 7 to 9 and comparative example 8 to 11 uses on average grain diameter and the uniformity as deposition materials outside, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 7 to 9 and comparative example 8 to 11.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 2.
Table 2
In table 2, dust/s means 0.1nm/s.
[preparation example 3: embodiment 10 to 12 and comparative example 12 to 15]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (C) with following structural formula, with preparation example 1 in the organic assembly deposition materials for embodiment 10 to 12 and comparative example 12 to 15 (preparation example 3) shown in same way as preparation table 3.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 3.
Compound (C)
(preparation of the organic electroluminescent device of preparation example 3)
Except the organic assembly deposition materials that contains the compound that serves as luminescent material (C) changed for embodiment 10 to 12 and comparative example 12 to 15 uses on average grain diameter and the uniformity as deposition materials, with preparation example 2 in the organic electroluminescent device of same way as Preparation Example 10 to 12 and comparative example 12 to 15.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 3.
Table 3
In table 3, dust/s means 0.1nm/s.
[preparation example 4: embodiment 13 to 15 and comparative example 16 to 19]
Except having, use suitably is selected from approximately 0.5 μ m to the about commercially available molybdenum trioxide (MoO of the particle diameter of the scope of 900 μ m
3the product of Furuuchi Chemical Corporation) replace serving as outside the compound (A) of grinding of material of main part, with preparation example 1 in the organic assembly deposition materials for embodiment 13 to 15 and comparative example 16 to 19 (preparation example 4) shown in same way as preparation table 4.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 4.
(preparation of the organic electroluminescent device of preparation example 4)
Except using mCP (two-carbazole benzene) as material of main part, and the organic assembly deposition materials of the molybdenum trioxide that contains the dopant that serves as hole injection layer changed in average grain diameter and the uniformity for embodiment 13 to 15 and comparative example 16 to 19 uses as deposition materials outside, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 13 to 15 and comparative example 16 to 19.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 4.
Table 4
In table 4, dust/s means 0.1nm/s.
[preparation example 5: embodiment 16 to 18 and comparative example 20 to 23]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (D) with following structural formula, with preparation example 1 in the organic assembly deposition materials for embodiment 16 to 18 and comparative example 20 to 23 (preparation example 5) shown in same way as preparation table 5.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 5.
Compound (D)
(preparation of the organic electroluminescent device of preparation example 5)
Except using mCP (two-carbazole benzene) as material of main part, and the organic assembly deposition materials that contains the compound that serves as luminescent material (D) changed in average grain diameter and the uniformity for embodiment 16 to 18 and comparative example 20 to 23 uses as deposition materials outside, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 16 to 18 and comparative example 20 to 23.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 5.
Table 5
In table 5, dust/s means 0.1nm/s.
[preparation example 6: embodiment 19 to 21 and comparative example 24 to 27]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (E) with following structural formula, with preparation example 1 in the organic assembly deposition materials for embodiment 19 to 21 and comparative example 24 to 27 (preparation example 6) shown in same way as preparation table 6.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 6.
Compound (E)
(preparation of the organic electroluminescent device of preparation example 6)
Except using mCP (two-carbazole benzene) as material of main part, and the organic assembly deposition materials that contains the compound that serves as luminescent material (E) changed in average grain diameter and the uniformity for embodiment 19 to 21 and comparative example 24 to 27 uses as deposition materials outside, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 19 to 21 and comparative example 24 to 27.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 6.
Table 6
In table 6, dust/s means 0.1nm/s.
[preparation example 7: embodiment 22 to 24 and comparative example 28 to 31]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (F) with following structural formula, with preparation example 1 in the organic assembly deposition materials for embodiment 22 to 24 and comparative example 28 to 31 (preparation example 7) shown in same way as preparation table 7.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 7.
Compound (F)
(preparation of the organic electroluminescent device of preparation example 7)
Except using mCP (two-carbazole benzene) as material of main part, and the organic assembly deposition materials that contains the compound that serves as luminescent material (F) changed in average grain diameter and the uniformity for embodiment 22 to 24 and comparative example 28 to 31 uses as deposition materials outside, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 22 to 24 and comparative example 28 to 31.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 7.
Table 7
In table 7, dust/s means 0.1nm/s.
[preparation example 8: comparative example 32 and 33]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (D) with top structural formula and does not carry out sublimation purification, with preparation example 1 in the deposition materials of the organic assembly for comparative example 32 and 33 (preparation example 8) shown in same way as preparation table 8.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 8.
(preparation of the organic electroluminescent device of preparation example 8)
Except using mCP (two-carbazole benzene) as material of main part, and for comparative example 32 and 33 use contain the compound that does not pass through sublimation purification (D) that serves as luminescent material changed in average grain diameter and the uniformity the organic assembly deposition materials as deposition materials outside, with preparation example 1 in same way as prepare the organic electroluminescent device of comparative example 32 and 33.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 8.
Table 8
In table 8, dust/s means 0.1nm/s.
As can be clearly from table 8, find to have the particle diameter that drops in desired scope and the uniformity poor on deposition rate stability but do not experience the organic assembly deposition materials of sublimation purification.Can the inhibition initial stage reduce and obtain stable deposition rate and become film uniformity by the impurity in the sublimation purification removing materials.
[preparation example 9: comparative example 34 and 35]
Except the compound (A) that will serve as material of main part is changed to the luminescent material of the compound (E) with top structural formula and does not carry out sublimation purification, with preparation example 1 in the deposition materials of the organic assembly for comparative example 34 and 35 (preparation example 9) shown in same way as preparation table 9.
The identical mode of carrying out with the organic assembly deposition materials with to preparation example 1 averages particle diameter and the uniformity, and the measurement of deposition rate, and the evaluation of deposition rate stability.Result provides in table 9.
(preparation of the organic electroluminescent device of preparation example 9)
Except using mCP (two-carbazole benzene) as material of main part, and for comparative example 34 and 35 use contain the compound that does not pass through sublimation purification (D) that serves as luminescent material changed in average grain diameter and the uniformity the organic assembly deposition materials as deposition materials outside, with preparation example 1 in same way as prepare the organic electroluminescent device of comparative example 34 and 35.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 9.
Table 9
In table 9, dust/s means 0.1nm/s.
As can be clearly from table 9, find to have the particle diameter that drops in desired scope and the uniformity poor on deposition rate stability but do not experience the organic assembly deposition materials of sublimation purification.Can the inhibition initial stage reduce and obtain stable deposition rate and become film uniformity by the impurity in the sublimation purification removing materials.
(preparation of the organic electroluminescent device of preparation example 10)
Except being the compound that serves as material of main part (A) that changes on average grain diameter and the uniformity as the organic assembly deposition materials of deposition materials and serve as the mixture of compound (E) under the mass ratio of 95: 5 of luminescent material, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 25 and comparative example 36.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 10.
Table 10
In table 10, dust/s means 0.1nm/s.
As can be clearly from table 10, the material with particle diameter defined above and uniformity can be made by homogenous material or multiple material.
(preparation of the organic electroluminescent device of preparation example 11)
Except being the compound that serves as material of main part (A) that changes on average grain diameter and the uniformity as the organic assembly deposition materials of deposition materials and serve as the mixture of compound (F) under the mass ratio of 90: 10 of luminescent material, with preparation example 1 in the organic electroluminescent device of same way as Preparation Example 26 and comparative example 37.
The resulting organic electroluminescent device assessment initial stage is reduced and become film uniformity in the mode with identical in preparation example 1.Result provides in table 11.
Table 11
In table 11, dust/s means 0.1nm/s.
As can be clearly from table 11, the material with particle diameter defined above and uniformity can be made by homogenous material or multiple material.
Industrial applicibility
The present invention can provide the organic assembly deposition materials and for using described organic assembly deposition materials to prepare the method for organic assembly, described method can be in the situation that the color stability that goes out of deposition rate be formed uniformly the large tracts of land film that contains organic compound, reduce the variation on the performance of organic assembly simultaneously, and therefore be suitable for the preparation of organic electroluminescence device, organic thin film solar cell and organic field effect tube.
Invoking marks
1 substrate
2 anodes
3 hole injection layers
4 hole transporting layers
5 luminescent layers
6 electron supplying layers
7 electron injecting layers
8 negative electrodes
10 organic electroluminescent devices
Claims (11)
1. the deposition materials for the preparation of organic assembly, described deposition materials has passed through sublimation purification, and forms organic layer by the flash deposition,
Wherein said deposition materials has the average grain diameter of 10 μ m to 200 μ m, and wherein said average grain diameter means by D50%, and described deposition materials has 1.0 to 3.5 the uniformity, and the wherein said uniformity means by D60% diameter/D10% diameter, and
Wherein said deposition materials is at least one in the group of selecting free luminescent material, material of main part and dopant material to form.
2. deposition materials according to claim 1, wherein said is 1.0 to 3.0 by the uniformity that the D60% diameter/the D10% diameter means.
3. deposition materials according to claim 1, wherein said deposition materials includes organic compounds or inorganic oxide.
4. deposition materials according to claim 3, wherein said deposition materials comprises two or more organic compounds.
5. deposition materials according to claim 1, wherein said deposition materials is used to form at least one organic layer arranged between the pair of electrodes of organic electroluminescent device.
6. deposition materials according to claim 1, wherein said organic layer is luminescent layer.
7. deposition materials according to claim 1, wherein said luminescent material comprises Ir complex or Pt complex.
8. deposition materials according to claim 1, wherein said material of main part comprises indole derivatives, carbazole derivates, aromatic uncle amine compound or thiophene derivant.
9. deposition materials according to claim 1, wherein said deposition materials is to have by following structural (A), (B), (C), (D), (E) or the compound of the structure (F) meaned:
Structural formula (A)
Structural formula (B)
Structural formula (C)
Structural formula (D)
Structural formula (E)
Structural formula (F).
10. the method for the preparation of organic assembly, described method comprises:
Deposition materials is passed through to the flash deposition to form organic layer,
Wherein said deposition materials is for the preparation of organic assembly, and described deposition materials has passed through sublimation purification, and forms organic layer by the flash deposition,
Wherein said deposition materials has the average grain diameter of 10 μ m to 200 μ m, and wherein said average grain diameter means by D50%, and described deposition materials has 1.0 to 3.5 the uniformity, and the wherein said uniformity means by D60% diameter/D10% diameter, and
Wherein said deposition materials is at least one in the group of selecting free luminescent material, material of main part and dopant material to form.
11. an organic assembly, described organic assembly obtains by the method for the preparation of organic assembly, and described method comprises:
Deposition materials is passed through to the flash deposition to form organic layer,
Wherein said deposition materials is for the preparation of organic assembly, and described deposition materials has passed through sublimation purification, and forms organic layer by the flash deposition,
Wherein said deposition materials has the average grain diameter of 10 μ m to 200 μ m, and wherein said average grain diameter means by D50%, and described deposition materials has 1.0 to 3.5 the uniformity, and the wherein said uniformity means by D60% diameter/D10% diameter, and
Wherein said deposition materials is at least one in the group of selecting free luminescent material, material of main part and dopant material to form.
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| JP2009219311 | 2009-09-24 | ||
| JP2009-219311 | 2009-09-24 | ||
| PCT/JP2010/062538 WO2011013626A1 (en) | 2009-07-31 | 2010-07-26 | Vapor deposition material for organic device and method for manufacturing organic device |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5662893B2 (en) * | 2011-07-25 | 2015-02-04 | 富士フイルム株式会社 | Vapor deposition material for photoelectric conversion element, photoelectric conversion element, sensor, imaging element |
| KR20140140417A (en) * | 2013-05-29 | 2014-12-09 | 삼성디스플레이 주식회사 | Organic light emitting diode |
| JP6111171B2 (en) * | 2013-09-02 | 2017-04-05 | 東京エレクトロン株式会社 | Film forming method and film forming apparatus |
| KR20160049974A (en) * | 2014-10-28 | 2016-05-10 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Light-emitting element, light-emitting device, electronic device, and lighting device |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2755945B2 (en) * | 1987-02-18 | 1998-05-25 | 旭硝子株式会社 | Manufacturing method of indium oxide sintered body containing tin for physical vapor deposition |
| JPH04268067A (en) * | 1991-02-20 | 1992-09-24 | Anelva Corp | Powder supplying device |
| JPH05178614A (en) * | 1991-12-11 | 1993-07-20 | Ishikawajima Harima Heavy Ind Co Ltd | Production of oxide superconductor film and equipment therefor |
| JPH06161137A (en) * | 1992-11-18 | 1994-06-07 | Fuji Electric Co Ltd | Manufacture of electrophotographic selenium photosensitive body |
| JPH07326801A (en) * | 1994-06-01 | 1995-12-12 | Matsushita Electric Ind Co Ltd | Manufacture of thin film thermoelectric material |
| JP3528470B2 (en) | 1995-10-27 | 2004-05-17 | 株式会社豊田中央研究所 | Micro-optical resonator type organic electroluminescent device |
| JPH09219289A (en) * | 1996-02-09 | 1997-08-19 | Chisso Corp | Organic thin film electroluminescent element and its manufacture |
| US6197218B1 (en) * | 1997-02-24 | 2001-03-06 | Superior Micropowders Llc | Photoluminescent phosphor powders, methods for making phosphor powders and devices incorporating same |
| JP3640512B2 (en) | 1997-09-24 | 2005-04-20 | 出光興産株式会社 | Vapor deposition method and organic electroluminescence device manufacturing method |
| US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| JP3586551B2 (en) | 1998-01-27 | 2004-11-10 | 松下電器産業株式会社 | Method and apparatus for manufacturing optical recording medium |
| US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
| US6207239B1 (en) * | 1998-12-16 | 2001-03-27 | Battelle Memorial Institute | Plasma enhanced chemical deposition of conjugated polymer |
| BRPI0009215B1 (en) | 1999-03-23 | 2017-05-09 | Univ Southern California | cyclometallized metal complexes as phosphorescent dopants in organic light-emitting diodes |
| KR100913568B1 (en) | 1999-05-13 | 2009-08-26 | 더 트러스티즈 오브 프린스턴 유니버시티 | Very high efficiency organic light emitting devices based on electrophosphorescence |
| US6310360B1 (en) | 1999-07-21 | 2001-10-30 | The Trustees Of Princeton University | Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices |
| US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
| KR100890980B1 (en) | 1999-12-01 | 2009-03-27 | 더 트러스티즈 오브 프린스턴 유니버시티 | Organic light emitting device comprising a phosphorescent organo metallic compound |
| JP3929690B2 (en) | 1999-12-27 | 2007-06-13 | 富士フイルム株式会社 | Light emitting device material, light emitting device and novel iridium complex comprising orthometalated iridium complex |
| JP3929706B2 (en) | 2000-02-10 | 2007-06-13 | 富士フイルム株式会社 | Light emitting device material and light emitting device comprising iridium complex |
| JP2001298470A (en) | 2000-04-11 | 2001-10-26 | Dx Antenna Co Ltd | Data transmission system |
| US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| JP4340401B2 (en) | 2000-07-17 | 2009-10-07 | 富士フイルム株式会社 | Light emitting device and iridium complex |
| CN102041001B (en) | 2000-08-11 | 2014-10-22 | 普林斯顿大学理事会 | Organometallic compounds and emission-shifting organic electrophosphorescence |
| JP4505162B2 (en) | 2000-09-21 | 2010-07-21 | 富士フイルム株式会社 | Light emitting device and novel rhenium complex |
| JP4067286B2 (en) | 2000-09-21 | 2008-03-26 | 富士フイルム株式会社 | Light emitting device and iridium complex |
| JP4086498B2 (en) | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | Metal coordination compound, light emitting device and display device |
| JP4086499B2 (en) | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | Metal coordination compound, light emitting device and display device |
| KR100798562B1 (en) | 2000-11-30 | 2008-01-31 | 캐논 가부시끼가이샤 | Luminescent Element and Display |
| JP4154145B2 (en) | 2000-12-01 | 2008-09-24 | キヤノン株式会社 | Metal coordination compound, light emitting device and display device |
| JP2002203678A (en) | 2000-12-27 | 2002-07-19 | Fuji Photo Film Co Ltd | Light-emitting element |
| JP2002203679A (en) | 2000-12-27 | 2002-07-19 | Fuji Photo Film Co Ltd | Light-emitting element |
| JP3812730B2 (en) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | Transition metal complex and light emitting device |
| JP3988915B2 (en) | 2001-02-09 | 2007-10-10 | 富士フイルム株式会社 | Transition metal complex, light emitting device material comprising the same, and light emitting device |
| US6797314B2 (en) | 2001-07-03 | 2004-09-28 | Eastman Kodak Company | Method of handling organic material in making an organic light-emitting device |
| JP2003123982A (en) | 2001-08-07 | 2003-04-25 | Fuji Photo Film Co Ltd | Light emitting element and novel iridium complex |
| TW595012B (en) * | 2001-09-03 | 2004-06-21 | Matsushita Electric Ind Co Ltd | Semiconductor light-emitting device, light-emitting apparatus and manufacturing method of semiconductor light-emitting device |
| EP1492768A1 (en) * | 2002-03-28 | 2005-01-05 | Basf Aktiengesellschaft | Phenethylacrylamide, methods for the production thereof and agents containing the same |
| JP3703028B2 (en) | 2002-10-04 | 2005-10-05 | ソニー株式会社 | Display element and display device using the same |
| JP4524093B2 (en) | 2002-12-17 | 2010-08-11 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4365199B2 (en) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4945057B2 (en) | 2002-12-27 | 2012-06-06 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4365196B2 (en) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP2004327313A (en) | 2003-04-25 | 2004-11-18 | Fuji Photo Film Co Ltd | Organic el device |
| EP3211057B2 (en) | 2003-06-02 | 2022-11-02 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
| JP2004357791A (en) | 2003-06-02 | 2004-12-24 | Sea Shell:Kk | Footwear |
| DE10338550A1 (en) | 2003-08-19 | 2005-03-31 | Basf Ag | Transition metal complexes with carbene ligands as emitters for organic light-emitting diodes (OLEDs) |
| DE10350722A1 (en) | 2003-10-30 | 2005-05-25 | Covion Organic Semiconductors Gmbh | metal complexes |
| CN1998087B (en) | 2004-03-12 | 2014-12-31 | 独立行政法人科学技术振兴机构 | Amorphous oxide and thin film transistor |
| US20050281948A1 (en) * | 2004-06-17 | 2005-12-22 | Eastman Kodak Company | Vaporizing temperature sensitive materials |
| US20060083694A1 (en) * | 2004-08-07 | 2006-04-20 | Cabot Corporation | Multi-component particles comprising inorganic nanoparticles distributed in an organic matrix and processes for making and using same |
| JP4500735B2 (en) | 2004-09-22 | 2010-07-14 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4531509B2 (en) | 2004-09-27 | 2010-08-25 | 富士フイルム株式会社 | Light emitting element |
| JP5138163B2 (en) | 2004-11-10 | 2013-02-06 | キヤノン株式会社 | Field effect transistor |
| JP4399382B2 (en) | 2005-03-16 | 2010-01-13 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4399429B2 (en) | 2005-03-16 | 2010-01-13 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP5046548B2 (en) | 2005-04-25 | 2012-10-10 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP2007084635A (en) | 2005-09-21 | 2007-04-05 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, organic electroluminescent element, display device and lighting equipment |
| JP4727684B2 (en) | 2007-03-27 | 2011-07-20 | 富士フイルム株式会社 | Thin film field effect transistor and display device using the same |
| JP5586843B2 (en) | 2007-11-27 | 2014-09-10 | ユー・ディー・シー アイルランド リミテッド | Organic electroluminescence device |
| JP5553763B2 (en) * | 2008-09-24 | 2014-07-16 | 出光興産株式会社 | Composite organic electroluminescent material |
| US8425801B2 (en) * | 2009-04-10 | 2013-04-23 | Idemitsu Kosan Co., Ltd. | Composite organic electroluminescent material and production method thereof |
-
2010
- 2010-07-26 WO PCT/JP2010/062538 patent/WO2011013626A1/en active Application Filing
- 2010-07-26 EP EP10804372A patent/EP2461387A4/en not_active Withdrawn
- 2010-07-26 CN CN2010800331451A patent/CN102473854B/en active Active
- 2010-07-26 KR KR1020127004448A patent/KR101235776B1/en active IP Right Grant
- 2010-07-26 US US13/387,982 patent/US20120135239A1/en not_active Abandoned
- 2010-07-30 TW TW099125371A patent/TWI486467B/en active
- 2010-07-30 JP JP2010171610A patent/JP4801211B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2461387A1 (en) | 2012-06-06 |
| TWI486467B (en) | 2015-06-01 |
| KR20120030163A (en) | 2012-03-27 |
| KR101235776B1 (en) | 2013-02-21 |
| EP2461387A4 (en) | 2013-01-23 |
| CN102473854A (en) | 2012-05-23 |
| JP2011091025A (en) | 2011-05-06 |
| US20120135239A1 (en) | 2012-05-31 |
| WO2011013626A1 (en) | 2011-02-03 |
| JP4801211B2 (en) | 2011-10-26 |
| TW201116638A (en) | 2011-05-16 |
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